Hydrochloric Acid → 5-(4-Phenoxyphenyl)-1,3-diazinane-2,4,6-trione

HRID 1386642ノート

反応式

HRID 1386642 の反応式
O(C)[Na].[O:4]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:22]([O:24]C)=O)[C:18]([O:20]C)=O)=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:26][C:27]([NH2:29])=[O:28].Cl>>[O:4]([C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[C:18](=[O:20])[NH:29][C:27](=[O:28])[NH:26][C:22]2=[O:24])=[CH:15][CH:16]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 15540880Dimethyl 2-(4-phenoxyphenyl)malonateHCID 178418582HCID 178418582、化合物

生成物 1

HCID 116737785-(4-Phenoxyphenyl)-1,3-diazinane-2,4,6-trione収率 84.1%

反応条件

温度
0 °C

実験手順

To a NaOCH3 solution (prepared by allowing 0.23 g of Na metal to react with 7.2 mL dry CH3OH) was added dimethyl 2-(4-phenoxyphenyl)malonate (1.0 g, 3.33 mmol) followed by urea (0.4 g, 6.66 mmol). The resulting white reaction mixture was refluxed for 24 hours and then cooled to 0° C. and acidified with 3N HCl. The white solids were filtered and washed with water and dried to give 900 mg of crude product. This was further purified by trituration with EtOAc/hexanes (1:1) to afford 5-(4-phenoxyphenyl)pyrimidine-2,4,6-trione as a white powder (830 mg): 1H NMR (400 mHz, CDCl3) 3:2 keto/enol form δ 11.38 (2×NH keto form, s), 10.58 (2×NH enol form, s), 7.46-6.91(9H, m), 4.85 (H-5, s); HRMS Calcd for C16H12N2O4 296.0796; Found 296.0806.

後処理

  1. temperatureThe resulting white reaction mixture was refluxed for 24 hours
  2. filtrationThe white solids were filtered
  3. washwashed with water
  4. customdried
  5. customto give 900 mg of crude product
  6. customThis was further purified by trituration with EtOAc/hexanes (1:1)

出典と根拠

ORDレコード
ord-29594cba50a449509d2aab90175e8084
出典データセット
uspto-grants-2001_07
特許番号
US06265578B1

反応ノート

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